Pondering Contentment

I guess this whole idea of contentment has been stirring in me for weeks. What is it? What does it mean? Why am I so scared to be content in areas of my life?
Growing up, materialism ruled in my life bigtime. I loved the stuff I had, but wasn't satisfied with it, I wanted more. I grew up in a family who had a lot of stuff and every time I turned around, we were selling it or buying it. Today however, that has since changed in me. Now I look around at my stuff and think to myself, "Now, what can I get rid of/live without?" !
Contentment. Oh how it used to scare me to pray for it. It scared me to be content with my singleness. If I was content, would that mean God would never let me be with "the one"? Does he even have one picked out for me? I was made fun of, picked on so much as a kid, the way I looked, walked... I believe that is what sparks the latter questions. I have a hard time believing it when people tell me He does have someone in mind for me.
I made a mention of my singleness in a previous post and received a reply from a friend who made such comments as "God said we aren't ripe yet" and "just waiting for Him to pick us like some fat cantaloupe." the phrase "fat cantaloupe" made me crack up laughing for some reason.
I read books by Elizabeth Elliot and Joshua Harris. Books on dating to me were the closest thing I had to dating, and I read them, and read them, and read them whenever I felt the longing inside me. Today, I reach for my Bible. Joshua Harris's book only made me smarter in the choices I make for what I wanted in a relationship. Going from "don't care if he's a Christian or not", to "being a Christian is the only requirement", to still even "okay, a few things in common is good enough", even now reading all that God would have us require in a future spouse and not knowing what I want because what I used to want doesn't even seem to matter anymore. I never did want someone who used a wheelchair like I do. God knows I fell for someone like that at one time. But he responded to a friend of mine (right in front of me!) "she's funny, but..." and didn't bother to finish the sentence. (Ouch!) I wanted him to be my date for the senior prom, though he went to a different school. He supposedly was taking another girl to her prom that night. That was the first and last time I ever had the nerve to do the asking.
I hear of people getting exactly what they want in their spouse and people saying to ask for these specific things and God will give it down to the last detail, I just wish I had the faith to believe that right now. I often hear people telling singles "Don't settle".
I can identify with some of El Blogo De Lafalda's blogpost 'Pondering loneliness' and her questions "what is this thing? Why does it hurt so deeply? What is its purpose? Is it simply a means to make us seek God? ...How can I be surrounded by the best friends in the world and still feel so alone?" and one of my own "What is God's purpose in allowing us to walk through it?"
Living in the Chi Alpha house was amazing the first year. I lay in bed after the night's house meeting thanking God for getting me involved, and for each person that lived here. Then, I was in attendance for the weddings of two now former roomies and got to thinking-"will I ever..." , secretly hoping my living in community wouldn't last for long. But at the same time, not wanting Chi Alpha to lose the house because mom and dad said that if I ever moved out, it would be sold.

Speaking of weddings, I can't help but sit through a wedding and daydream of my own. I once had a file on my computer that listed ideas for an ideal wedding, but erased it for some reason I still don't understand. Maybe it was a God thing.
Tired of this longing in me, I have asked God on numerous occasions to take it away yet only for it to grow stronger.
I have been praying into a prophecy spoken over me a few years ago. I was at a Chi Alpha retreat and a young girl in our fellowship had planned for the speaker we were to have. The speaker is a good friend of her family's and was gifted in prophecy. "Don't be afraid to love" was just one of the statements she made to me. The statement left me wondering, "what does this mean!?"

And no, I didn't write this all in one day.